RU2012120614A - NEW BACITRACINE ANTIBIOTICS - Google Patents
NEW BACITRACINE ANTIBIOTICS Download PDFInfo
- Publication number
- RU2012120614A RU2012120614A RU2012120614/04A RU2012120614A RU2012120614A RU 2012120614 A RU2012120614 A RU 2012120614A RU 2012120614/04 A RU2012120614/04 A RU 2012120614/04A RU 2012120614 A RU2012120614 A RU 2012120614A RU 2012120614 A RU2012120614 A RU 2012120614A
- Authority
- RU
- Russia
- Prior art keywords
- compound according
- compound
- pharmaceutical composition
- isoleucine
- bacitracine
- Prior art date
Links
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 title claims abstract 3
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 229940088710 antibiotic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- FAQNEUQXEJMKEU-WDSKDSINSA-N (2s,3s)-2-amino-3-methylhex-5-enoic acid Chemical compound C=CC[C@H](C)[C@H](N)C(O)=O FAQNEUQXEJMKEU-WDSKDSINSA-N 0.000 claims abstract 2
- 108010001478 Bacitracin Proteins 0.000 claims abstract 2
- 208000035143 Bacterial infection Diseases 0.000 claims abstract 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical group CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims abstract 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical group CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims abstract 2
- 229960003071 bacitracin Drugs 0.000 claims abstract 2
- 229930184125 bacitracin Natural products 0.000 claims abstract 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract 2
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 150000004677 hydrates Chemical class 0.000 claims abstract 2
- 238000000338 in vitro Methods 0.000 claims abstract 2
- 229960000310 isoleucine Drugs 0.000 claims abstract 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims abstract 2
- 230000001225 therapeutic effect Effects 0.000 claims abstract 2
- 239000004474 valine Chemical group 0.000 claims abstract 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
- C07K7/58—Bacitracins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/03—Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1. Соединение, представленное формулойгдепо меньшей мере один из R, Rи Rпредставляет собой -CH=CH, и гдеR, Rи Rнезависимо представляют собой -H, -CHили -CH=CH, и его соли и гидраты.2. Соединение по п.1, где один из R, Rи Rпредставляет собой -CH.3. Соединение по п.1, где два из R, Rи Rпредставляют собой -CH.4. Соединение по п.1, где Rпредставляет собой -CH=CH.5. Соединение по п.1, где Rпредставляет собой -CH=CH.6. Соединение по п.1, где Rпредставляет собой -CH=CH.7. Соединение по п.1, где Rи Rпредставляют собой -CH=CH.8. Соединение по п.1, где Rи Rпредставляют собой -CH=CH.9. Соединение по п.1, где Rи Rпредставляют собой -CH=CH.10. Соединение по п.1, где R, Rи Rпредставляют собой -CH=CH.11. Композиция, содержащая соединение по п.1.12. Фармацевтическая композиция, содержащая соединение по п.1.13. Фармацевтическая композиция по п.12, обладающая терапевтическим эффектом.14. Применение соединения по п.1 для изготовления лекарственного средства для лечения бактериальных инфекций.15. Способ получения соединений по п.1 путем замещения изолейцина или валина на 5-метилен-изолейцин при синтезе in vitro бацитрацина.1. The compound represented by the formula wherein at least one of R, R and R is —CH═CH, and wherein R, R and R are independently —H, —CH or —CH = CH, and its salts and hydrates. 2. A compound according to claim 1, wherein one of R, R and R is —CH. 3. The compound of claim 1, wherein two of R, R and R are —CH. 4. The compound according to claim 1, where R is -CH = CH.5. The compound according to claim 1, where R is -CH = CH.6. The compound according to claim 1, where R is -CH = CH.7. The compound of claim 1, wherein R and R are —CH = CH. A compound according to claim 1, wherein R and R are —CH = CH. A compound according to claim 1, wherein R and R are —CH═CH.10. The compound of claim 1, wherein R, R and R are —CH═CH.11. A composition comprising a compound according to Claim 1.12. A pharmaceutical composition comprising a compound according to claim 13. The pharmaceutical composition according to claim 12, having a therapeutic effect. The use of a compound according to claim 1 for the manufacture of a medicament for the treatment of bacterial infections. The method of producing compounds according to claim 1 by substituting isoleucine or valine for 5-methylene-isoleucine in the synthesis of in vitro bacitracin.
Claims (15)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25551709P | 2009-10-28 | 2009-10-28 | |
| US61/255,517 | 2009-10-28 | ||
| PCT/EP2010/064523 WO2011051073A1 (en) | 2009-10-28 | 2010-09-30 | New bacitracin antibiotics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012120614A true RU2012120614A (en) | 2013-12-10 |
| RU2536588C2 RU2536588C2 (en) | 2014-12-27 |
Family
ID=43417043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012120614/04A RU2536588C2 (en) | 2009-10-28 | 2010-09-30 | New bacitracin antibiotics |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US8410044B2 (en) |
| EP (1) | EP2493493B1 (en) |
| JP (1) | JP5763082B2 (en) |
| KR (1) | KR20120097379A (en) |
| CN (1) | CN102596218B (en) |
| AU (1) | AU2010311762B2 (en) |
| BR (1) | BR112012009943A2 (en) |
| CA (1) | CA2774590A1 (en) |
| CY (1) | CY1118233T1 (en) |
| DK (1) | DK2493493T3 (en) |
| ES (1) | ES2588205T3 (en) |
| HR (1) | HRP20161020T1 (en) |
| HU (1) | HUE029412T2 (en) |
| IL (1) | IL219183A (en) |
| IN (1) | IN2012DN01971A (en) |
| LT (1) | LT2493493T (en) |
| PL (1) | PL2493493T3 (en) |
| PT (1) | PT2493493T (en) |
| RU (1) | RU2536588C2 (en) |
| SI (1) | SI2493493T1 (en) |
| WO (1) | WO2011051073A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2493843T3 (en) * | 2009-10-28 | 2016-01-25 | Xellia Pharmaceuticals Aps | 2-amino-3-methyl-hex-5-enoic acid and their use in the preparation of peptides, such as bacitracins |
| CN109444318B (en) * | 2018-12-03 | 2021-04-27 | 上海市食品药品检验研究院 | High performance liquid chromatography method for analyzing bacitracin component |
| CN111057131A (en) * | 2019-12-13 | 2020-04-24 | 上海市食品药品检验所 | Bacitracin and analysis method of components thereof |
| CN111678996A (en) * | 2020-04-26 | 2020-09-18 | 上海市食品药品检验所 | Bacitracin oxidized fraction, method for analyzing same, and fragmentation pattern of double-bond sulfonated cysteine oxidized fraction |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5300491A (en) | 1991-10-31 | 1994-04-05 | Apothekernes Laboratorium A.S. | Treatment of protozoal infection |
| WO1997047313A1 (en) | 1996-06-10 | 1997-12-18 | The Board Of Trustees Of The Leland Stanford Junior University | Total synthesis of bacitracin polypetides |
-
2010
- 2010-09-30 JP JP2012535720A patent/JP5763082B2/en not_active Expired - Fee Related
- 2010-09-30 CA CA2774590A patent/CA2774590A1/en not_active Abandoned
- 2010-09-30 CN CN201080048962.4A patent/CN102596218B/en not_active Expired - Fee Related
- 2010-09-30 US US13/502,142 patent/US8410044B2/en active Active
- 2010-09-30 KR KR1020127013675A patent/KR20120097379A/en not_active Abandoned
- 2010-09-30 SI SI201031258A patent/SI2493493T1/en unknown
- 2010-09-30 EP EP10765613.4A patent/EP2493493B1/en active Active
- 2010-09-30 ES ES10765613.4T patent/ES2588205T3/en active Active
- 2010-09-30 PT PT107656134T patent/PT2493493T/en unknown
- 2010-09-30 LT LTEP10765613.4T patent/LT2493493T/en unknown
- 2010-09-30 AU AU2010311762A patent/AU2010311762B2/en not_active Ceased
- 2010-09-30 WO PCT/EP2010/064523 patent/WO2011051073A1/en not_active Ceased
- 2010-09-30 PL PL10765613T patent/PL2493493T3/en unknown
- 2010-09-30 RU RU2012120614/04A patent/RU2536588C2/en not_active IP Right Cessation
- 2010-09-30 IN IN1971DEN2012 patent/IN2012DN01971A/en unknown
- 2010-09-30 HU HUE10765613A patent/HUE029412T2/en unknown
- 2010-09-30 HR HRP20161020TT patent/HRP20161020T1/en unknown
- 2010-09-30 DK DK10765613.4T patent/DK2493493T3/en active
- 2010-09-30 BR BR112012009943A patent/BR112012009943A2/en not_active IP Right Cessation
-
2012
- 2012-04-15 IL IL219183A patent/IL219183A/en not_active IP Right Cessation
-
2016
- 2016-08-25 CY CY20161100841T patent/CY1118233T1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CY1118233T1 (en) | 2017-06-28 |
| LT2493493T (en) | 2016-09-26 |
| RU2536588C2 (en) | 2014-12-27 |
| CN102596218A (en) | 2012-07-18 |
| JP2013509367A (en) | 2013-03-14 |
| WO2011051073A1 (en) | 2011-05-05 |
| IL219183A (en) | 2015-04-30 |
| PT2493493T (en) | 2016-08-31 |
| DK2493493T3 (en) | 2016-09-05 |
| US20120202737A1 (en) | 2012-08-09 |
| US8410044B2 (en) | 2013-04-02 |
| IL219183A0 (en) | 2012-06-28 |
| KR20120097379A (en) | 2012-09-03 |
| BR112012009943A2 (en) | 2019-09-24 |
| IN2012DN01971A (en) | 2015-08-21 |
| HRP20161020T1 (en) | 2016-10-21 |
| EP2493493B1 (en) | 2016-07-06 |
| CA2774590A1 (en) | 2011-05-05 |
| AU2010311762A1 (en) | 2012-03-29 |
| PL2493493T3 (en) | 2017-01-31 |
| JP5763082B2 (en) | 2015-08-12 |
| HUE029412T2 (en) | 2017-02-28 |
| ES2588205T3 (en) | 2016-10-31 |
| SI2493493T1 (en) | 2016-10-28 |
| EP2493493A1 (en) | 2012-09-05 |
| CN102596218B (en) | 2014-10-22 |
| AU2010311762B2 (en) | 2015-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20171001 |